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N,N'-Dicyclohexylcarbodiimide, commonly known as DCC, is an organic compound with the CAS number 538-75-0 and the chemical formula C13H22N2. It is a white crystalline solid that is used as a coupling agent in organic synthesis, particularly in the formation of peptide bonds and in the synthesis of esters. DCC is known for its effectiveness in promoting esterification reactions, a process where acids react with alcohols to form esters.
DCC is not soluble in water but is soluble in organic solvents such as benzene, ethanol, and ether. It has a melting point of 35-36°C and a boiling point of 154-156°C at 1.47kPa, and 98-100°C at 66.7kPa. The compound is often used in the synthesis of peptides and nucleic acids, and it is also utilized as a dehydrating agent in the production of acids, anhydrides, aldehydes, and ketones.
The mechanism of action involves the activation of carboxyl groups, making them more susceptible to nucleophilic attack by amines or alcohols, leading to the formation of amide or ester bonds, respectively. DCC is often used in conjunction with a catalyst such as 4-dimethylaminopyridine (DMAP) to increase the efficiency of the reaction.
In the laboratory, DCC is prepared through several methods, including the reaction of cyclohexylamine with carbon disulfide to form dicyclohexylthiourea, which is then treated to remove hydrogen sulfide.
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